He went freelance in 1981, producing work for magazines including Playboy, Rolling Stone and Vanity Fair. He is a proponent of gonzo journalism, his master-work in this genre being 1987's "How to Drive Fast on Drugs While Getting Your Wing-Wang Squeezed and Not Spill Your Drink". In 1987 his second book Republican Party Reptile (1986) became a bestseller, and he has since written nine more books (to CEO of the Sofa (2001). As the title Republican Party Reptile implies, his economic and geopolitical views are notably right-wing (which, for some reason, is rare amongst both writers and comedians), but his liberal views on sex and drugs would fit uncomfortably with many of his economic fellow-travellers. O'Rourke has, in fact, sarcastically proposed two other American political parties: one to cater those with his peculiar mixture of views, and another for those who hold the opposite mixture.

His other books are The Bachelor Home Companion (1987), Holidays in Hell (1988), Parliament of Whores (1991), Give War a Chance (1992), All the Trouble in the World (1994), Age and Guile Beat Youth, Innocence, and a Bad Haircut (1995), The American Spectator's Enemies List (1996), and Eat the Rich (1999).

He is currently the foreign-affairs desk chief for Rolling Stone magazine.

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